Jessie's Big Threesome
by sean.p.ware
Summary: Luke catches Jessie and Shaylee having sex and joins the fun with them. Set during Jessie's Big Break. Rated M for Sexual Content. P.S. I Do Not Own Jessie.
1. Chapter 1

**Jessie's Big Threesome**

**Hi everybody, sean. here bringing you my first M-rated **_**Jessie **_**story. This story takes place during the season two episode Jessie's Big Break. Jessie and Shaylee have their sleepover and they have their first lesbian experience. Luke films it on his phone and the two girls catch him and they let Luke join in on the fun. Jessie/Luke/Shaylee one-shot. Rated M for sexual content. P.S. I do not own **_**Jessie**_**.**

Jessie was excited to have Australian actress Shaylee Michaels over for a sleepover. The two became the best of friends. Ever since they first met at Central Park, Jessie felt sexually attracted to Shaylee. Since they're having a sleepover, they can do things together. Jessie has never kissed a girl before or fucked a girl, but with Shaylee she is going to have her first lesbian experience. The two were sitting up in Jessie's room as they began to talk to each other. They were talking about girl stuff like boys, chick flick and all that good stuff.

"Wow Jessie. Tonight has been a lot of fun." Said Shaylee.

"I know, I'm having so much fun with my new best friend." Said Jessie as she smiled at Shaylee.

"Me too." Said Shaylee. "So what do you want to do? We've watched a movie and ate popcorn. We also talked about boys and the men in our life."

"How about we play truth or dare." Said Jessie.

"Sounds like fun!" Exclaimed Shaylee. She was getting very excited about playing that game. Her and Jessie are going to have a lot of fun. Maybe Jessie can kiss Shaylee and maybe even fuck her. While the two teens have their little sleepover, Luke was spying on Jessie and Shaylee. He was hiding in Jessie's closet spying on his nanny and her new best friend to see if they are going to kiss each other.

"God! Come on you two, kiss each other." Luke groaned silently as he was waiting for some action from the two. The wait was killing him.

"Okay Shaylee, you go first." Said Jessie.

"Okay. Jessie, truth or dare?" Asked Shaylee.

"Truth." Said Jessie.

"Have you ever kissed a boy?" Asked Shaylee.

"Yes." Said Jessie.

"Now its your turn." Said Shaylee smiling.

"Shaylee, truth or dare?" Asked Jessie."

"Truth." Said Shaylee.

"Have you ever kissed a girl before?" Asked Jessie.

"No." Said Shaylee. "Alright Jessie, truth or dare?"

"Dare." Said Jessie. Shaylee was surprised to hear Jessie say "dare".

"Jessie, I dare you to kiss me." Said Shaylee. Luke was happy to hear Shaylee to tell Jessie to kiss her. He's been waiting for this moment to see Jessie and Shaylee kiss each other. Jessie started to move in closer to Shaylee and cupped her cheek gently and starts to kiss her. Luke felt like the luckiest guy in the world as he started to film the two girls kissing each other. The two continued to kiss each other as they both started to deepen the kiss. Shaylee reached her hand up and started to touch one of Jessie's breasts as Jessie started to gasp at the feeling while Luke is enjoying the show from the two. Shaylee started to pull back and gasp for air, leaving Luke disappointed.

"I'm sorry Jessie. I didn't know that I went to far." Said Shaylee as she started to blush.

"That's okay. I kinda liked that." Said Jessie. Shaylee smiled at Jessie and started to kiss her again. Luke started to get really happy seeing the two kiss again until he started to notice something huge in his pants, he was getting a boner. The sight of Jessie and Shaylee gave Luke an erection automatically. Shaylee started to unbutton Jessie's pajama top, revealing her beautiful D-cup breasts that were covered by her red lacy front-hooked bra and took off her pajama pants leaving her in her red-laced panties. Luke felt like masturbating to Jessie and Shaylee. Seeing his nanny in her bra panties really turned him on. The luscious redhead did the same with Shaylee as she started to take off her matching blue pajama top and pants, leaving her in her matching pink lacy-front hook bra with white polka dots and pink lacy polka dot panties. Luke stopped filming the two and started to unzip his pants and stuck his hand down and began to slowly stroke himself. Luke let out a moan as he continues to jerk himself off, using his pre-cum as a lube and started to enjoy the sensation. Jessie's tongue started to lick Shaylee's bottom lip, begging for entrance as she let Jessie in her mouth and began to battle her tongue for dominance. Both of their tongues were coated with each other's saliva as they both started to moan into the kiss. Shaylee slipped her hand down to Jessie's panties and gently rubbed her pussy. Jessie moaned into Shaylee's lips as she let her partner continue to pleasure her until they hear a moan that is not theirs coming from the closet. They stopped their heated makeout session to check out who's in the closet. Luke stopped masturbating and zipped up, he knew that he was going to get caught by the two. Jessie opened the closet door and she sees Luke zipping up his pants.

"Luke, what the fuck are you doing in my room?" Asked Jessie.

"I don't know. I've must've been sleepwalking." Said Luke.

"He's been spying on us making out." Said Shaylee.

"What? No I haven't." Said Luke.

"Luke." Said Jessie.

"Okay, I have been spying on you two kissing and doing more." Said Luke.

"Is your camera on your phone on?" Asked Shaylee.

"No." Said Luke. Jessie snatched the phone out of Luke's hand and saw that it was still on.

"You little pervert. You saw us." Said Jessie.

"So what. I can see some hot action from you two. It's not a crime for me to watch." Said Luke.

"Yes it is! You're being a peeping tom." Said Shaylee.

"Well I'll tell you what. You let me join in on your hot action and it will be between us." Said Luke.

"What? We're not going to have sex with you." Said Jessie.

"Okay, fine. I guess I won't be posting the video of you two kissing on the Internet. Also, the tabloids will pick it up; it will be on the news. Plus, Morgan and Christina will fire you, Jessie and Shaylee you would never work in Hollywood again. So what's it going to be?" Asked Luke. Jessie and Shaylee couldn't believe that Luke is blackmailing them. It's either having sex with Luke or lose their jobs.

"Fine, Luke. We'll have sex with you." Said Jessie. "What do you want us to do?"

"First thing I want you two to do. Shaylee, I want you to make love to Jessie." Said Luke. Shaylee started to kiss Jessie in a heated makeout session. Luke started to take off his shirt, shoes, socks and pants leaving him in only his boxers. Shaylee starts to unhook Jessie's bra from the front as she took a great look at her D-cup breasts.

"Your breasts look really sexy." Said Shaylee. Jessie laid down on the bed and let Shaylee do her magic. Shaylee started to kiss Jessie on her lips and to her neck hitting that special spot and moved down to her left breast, taking her light brown nipple and began to suck her nipple. She actress used her hand to start cupping Jessie's other breast gently and rolled her nipple between her nipple and pinching it, making Jessie moan in delight. After coating her left nipple with her saliva, Shaylee moved on to the other and did the same thing with the other.

"Mmm." Moaned Jessie as she continues to enjoy this hot pleasure from Shaylee. Luke took off his boxers and starts to stroke his 8-inch cock while Shaylee is making love to Jessie. Shaylee moved her tongue down to Jessie's stomach and started to lick around her belly button. She then proceeds to move down to her leg and began licking her foot. Luke was enjoying the sight of seeing his nanny's pretty toes getting sucked on, he wishes he could stick his hard cock between the soles of her feet and let her foot fuck him. After sucking on Jessie's toes, Shaylee took off Jessie's panties and saw how wet she was.

"Looks like you're really wet for me baby." Said Shaylee as she starts to lick Jessie's wet pussy slowly. Jessie's pussy was hairless; she kept herself presentable if she wants to have her first time with Tony. Luke went over to Jessie and Shaylee as he went behind Shaylee and unhooked her bra and gently starts to squeeze her C-cup breasts, making her moan into Jessie's pussy. Jessie started to moan to the feeling of Shaylee's tongue on her pussy.

"Oh Shaylee. That's so fucking hot." Moaned Jessie as Shaylee looked up into Jessie's beautiful brown eyes as she continues to eat her out. Luke then starts to remove Shaylee's panties, her lovely curved ass sticking up in the air for Luke as he begins to lick her pussy. Luke started to slowly suck on Shaylee's clit while she starts tongue-fucking Jessie.

"God, that feels so amazing." Jessie breathed. Shaylee started to moan into Jessie's wet slit while Luke was licking and fingering her. Jessie's moans start to intensify getting ready to cum.

"Mmm! Shaylee!" Screamed Jessie as she starts to cum into Shaylee's mouth. Her juices spilled out all over her tongue. After being eaten out by Shaylee, Jessie decides it's time for payback. Luke stopped licking Shaylee's pussy as he let her sit on Jessie's face. Jessie began to lick Shaylee's pussy that was still dripping with her cum while she held her legs up and let Luke lick her pussy. Luke was enjoying the taste of Jessie pussy, he fantasized about eating out his nanny and now that fantasy has become a reality.

"Oh Jessie." Moaned Shaylee. Jessie starts to moan into Shaylee's pussy while Luke is licking her pussy. After he finishes licking her pussy, Luke then starts to lick Jessie's tight little asshole. Jessie really enjoyed the feeling of Luke's tongue on her ass and his fingers in her dripping wet slit, it drove her really wild. Shaylee starts bouncing her ass up and down on Jessie's as she starts to moan uncontrollably.

"Oh god, I'm about to cum!" Cried Shaylee. After she came all over Jessie's face, Shaylee brought herself to her lips and began to kiss her tasting herself on Jessie's lips turning her on. Now, it was their turn to do Luke.

"Looks like you've been a naughty boy, Luke." Said Shaylee. The two teens laid Luke down and they brought out a carton of vanilla ice cream and whipped cream. Luke felt the cold shock of the ice cream on his crotch as he starts to watch them pleasure him. Jessie starts to put the whipped cream on Luke's cock as her and Shaylee begin to lick the ice cream off of his cock.

"Oh yeah, lick that ice cream off of my hot cock." Moaned Luke as he watches the girls of his dreams licking the ice cream off of him. The ice cream started to met and the whipped cream started melting with it as it starts to drip down Luke's asshole. Shaylee starts to lick Luke's ass while Jessie is licking the ice cream off and giving him a blowjob. Luke has never let a girl rimming him before but this is the first time and he's enjoying the sensation.

"Fuck, Shaylee. You're such a dirty little slut." Moaned Luke. It turned Shaylee on being called a dirty little slut. Jessie stuck her D-cup breasts inbetween Luke's cock and began to titfuck him. A rimjob from Shaylee and a titfuck from Jessie, Luke was really having the time of his life. Luke was close to cumming, he desperately wanted to fuck both Jessie and Shaylee right now.

"Jessie, I want to be inside you right now." Said Luke as he rolled Jessie over on her back. Jessie spread her legs wide and held them open as Luke lined up his cock with her entrance as he slowly starts fucking her, breaking her hymen. Jessie started to feel a bit of pain when Luke penetrated her, getting a few inches in. After feeling a bit a pain, she felt pleasure. Shaylee starts to watch Luke fucking Jessie while she starts to rub her pussy.

"Harder." Moaned Jessie. Luke started to fuck Jessie harder.

"Faster, baby." She moaned as the young dancer starts to fuck her hard and fast. Shaylee begins to finger dripping wet box hard

"Oh shit, Luke. You're so big in me." Moaned Jessie. Luke got completely on top of Jessie as she wrapped her legs around his waist and her hands on his back as he fucked her in a missionary position. They fucked for a few good minutes until Jessie was ready to cum.

"I'm cumming Luke!" Yelled Jessie.

"Cum for me Jessie. I want you to cum all over this big cock. Squirt all over me." Said Luke. Jessie started to cum really hard and squirted all over Luke's cock. She started to shiver and twitch after her intense orgasm. Now, it's Shaylee's turn to get fucked by Luke as she starts to bend over and Luke started to enter Shaylee's pussy nice and slow while he's kissing Jessie.

"God, Shaylee. You feel so tight." Said Luke as he continues to fuck Shaylee. Shaylee started to moan to the feeling of Luke's cock inside her while Jessie watches and fondles her breasts. Luke started to go faster and harder, making Shaylee enjoy this hot pleasure.

"Oh Luke, that feels so good. I wanna cum all over you." Shaylee moaned as Jessie begins to kiss her. Luke starts to rub Shaylee's clit and gently pinching it, driving her over the edge she was ready to cum and so was Luke.

"Mmm, Oh god, I'm about to cum!" Screamed Shaylee as she starts to cum all over Luke's cock. Luke pulled out of her pussy after she came and Jessie and Shaylee both start to suck on his cock as he was ready to blow his load in Jessie's mouth.

"Oh Jessie! AHHHH!" Yelled Luke as he came hard into Jessie's mouth. He shot his hot load into his nanny's mouth and she shared it with Shaylee and swallowed it all. The three were feeling exhausted as they start to cuddle with each other and drifted to sleep.

"Luke." Said Jessie.

"Yes, Jessie." Said Luke.

"Don't tell your friends at school. This stays between us." Said Jessie.

"Don't worry Jessie. It will be our little secret." Said Luke.

**So that was my attempt for my 1****st**** M-rated Jessie story. So what did you think? Make sure you review the story (No Bad Reviews) and don't forget to check out my other stories. Till next time my fellow readers.**


	2. Chapter 2

**Jessie's Big Threesome Part 2**

**Hey everybody, sean. here bringing you another hot chapter of this great story Hope you enjoy it. **

**Chapter Two**

Luke was sitting in his room playing video games. Still thinking about his hot night with Jessie and Shaylee, it was a hot night to remember and he was hoping to do it again. While Luke was playing video games, Jessie and Shaylee entered the room to surprise him.

"Oh Luke. We have a surprise for you." Said Jessie in a seductive tone.

"What is it, Jessie?" Asked Luke as he turned off his game and started to look at Jessie and Shaylee. They were both dressed up in a schoolgirl uniform and when Luke saw the two teenage girls, he thought that they both looked really sexy. He wants to take them right now and seduce them.

"So what do you think?" Asked Shaylee.

"You two look really sexy." Said Luke as he got up from the floor. When Jessie began to kiss Shaylee and fondling her beautiful C-cup breasts, Luke started to get a raging hard-on and it was making him very horny, seeing Jessie and Shaylee kiss each other and wanted to masturbate right in front of them so bad it's driving him wild. Jessie and Shaylee started to notice Luke's hard-on and wanting to do something about it.

"Luke, looks like you need a little help with that." Said Jessie.

"Yes I do." Said Luke. "I have a wild idea for us. Jessie, how about I seduce you and strip you naked while Shaylee watches us. Then, Shaylee can come and join us for some hot fun."

"Sounds like a naughty idea." Said Shaylee.

"Yeah, it sure does. Go ahead Luke, have your way with me." Said Jessie. Luke began to kiss Jessie passionately while Shaylee starts to strip out of her schoolgirl uniform. Shaylee unbuttons her shirt and removed it from her body, reavealing her black lacy front-hooked bra and began to unhook it and gently squeezing her beautiful voluptuous breasts. Luke slowly unbuttoned Jessie's shirt and let it drop to the ground while squeezing her breasts that were still covered by her pink lacy bra. Luke began to remove Jessie's skirt and her pink lacy panties and laid her on the bed. Luke removed Jessie's stockings off of her sexy legs and took a good long look at her beautiful naked body.

"You're so beautiful, Jessie." Said Luke.

"Mmm, take me now you naughty boy." Said Jessie. Luke began to lay Jessie on the bed as Shaylee came over to the bed and shared a passionate kiss with Jessie while Luke was sucking on Jessie beautiful breasts. Luke took Jessie's light brown nipple and began to lick it passionately, making Jessie moan into the kiss as she begins to remove Shaylee's skirt and her stockings. Now, both girls are completely naked. Jessie took one of Shaylee's breasts and begin to lick her nipple while she uses her other hand to fondle with the other breast. While Jessie was pleasuring Shaylee, Luke continues to kiss down Jessie's nude body and spread her legs wide and began to eat her out. Jessie felt Luke's wet tongue touching her pussy as she started to moan. Shaylee began to sit on Jessie's face on top of her and began to lick her. Jessie saw how wet Shaylee was; her pussy was dripping with her wetness and she wanted to taste her and let her cum in her mouth. Jessie licked around Shaylee's folds and inserted her tongue into her pussy. Both girls were close to cumming and one of them is going to cum first. Luke gently pinched Jessie's pussy and Shaylee starts to hump Jessie's face and she was close to her climax.

"Oh god! Jessie, I'm cumming!" Screamed Shaylee as she came all over Jessie's face. Her sweet juices spilled out of her pussy and went into Jessie's mouth. Jessie came all over Luke's mouth and Luke started to lick up all of her cum. Now, two girls want to have a piece of Luke and his 'tool' as Jessie and Shaylee laid Luke on the bed and removed his shirt and his jeans. Jessie removed Luke's socks and his red briefs as his 9-inch cock sprung out.

"Ooh Luke. Looks like you're really hard for us." Said Jessie.

"You and Shaylee will have to fight for it." Said Luke.

"We don't have too." Said Shaylee. Jessie began to lick Luke's cock passionately while Shaylee licks his balls. Luke began to moan to the feeling of Jessie and Shaylee pleasuring him. Jessie placed her hand on Luke's hardness and started to stroke it while Shaylee licks the tip of my cock. After jerking me off for a minute, Jessie starts to suck on Luke hardened 'tool'. The sounds of her slurping filled the room as she went down on him. Her beautiful green eyes never lost her lock on Luke's eyes. Jessie wanted to do the same thing that Shaylee did to Luke last night. With Shaylee watching her pleasuring Luke, Jessie grabbed Luke's legs and pushed them onto the bed and began to lick his puckered asshole.

"Oh shit. Looks like someone's a dirty little slut." Said Luke as Jessie continues licking his back hole. Shaylee took her hand and began to jerk him off while Jessie is rimming him. Luke was caught off-guard when Shaylee placed a passionate kiss on his lips. Jessie moved away from Luke's ass as she lowered herself on Luke's wet cock that was covered with her saliva. Jessie took his whole dick into her pussy and slowly began to ride him while Shaylee comes up behind her and play with her clit.

"Mmm Luke." Moaned Jessie.

"You're so horny for me Jessie." Said Shaylee as she continues to rub Jessie's clit in a circular motion. Jessie began to ride Luke's cock faster while Shaylee plays with her clit faster as Jessie's moans begin to intensify. Luke begins to watch as Jessie and Shaylee were making out with each other while she was being fucked and Luke and Shaylee knew that Jessie was close to her climax and Luke was nearing the edge too as he felt himself feeling ready to blow his load and the feeling of Jessie's cum surrounding his cock.

"Ahh! Oh shit, Luke. I'm cumming!" Yelled Jessie.

"Cum for daddy, baby. Cum for daddy." Said Luke. Jessie started to cum all over Luke's cock and got off of him and laid down while Luke brought himself over to her and began to jerk himself off and shoot his load all over Jessie's breasts. Shaylee starts to lick Luke's giant, creamy white load off of Jessie's breasts and shared his cum with Jessie. Jessie did the most sexiest thing in front of Luke and Shaylee, she took Luke's cum and swallowed his whole load.

"God Jessie. That was hot." Said Luke. "I'm glad that I had this really hot day with you two."

**So what did you think of this chapter? Sorry it took me so long to update this story. I have been having trouble with the network at where I live. Don't forget to review this story (No Bad Reviews) and I'll see you guys later. Till next time my fellow readers.**


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